In the 18th and 19th centuries the land on the south side of the bend in the Glossop Brook, from the Centre of Howard Town to Wren Nest, was originally known as Hare Hill Wood and the wooded area there was apparently a place where bare-knuckle prize-fighting took place, probably in the early 19th century.

Until the late 1880's Glossop Brook ran in the open along the back of the new Town Hall and Market Hall, crossed only by the bridge on the turnpike road from Chapel-en-le-Frith. At that time Market Street stopped at the Bridge Inn [now Lomas's offices].

The bridge at Bridge End, to give it its old 18th century name, in the area later to be renamed Howard Town, was originally a pack-saddle bridge. It was widened and otherwise improved, especially its approach roads which were very steep on the Whitfield side. The old Turnpike road was to the east of the present bridge, went up Smithy Fold and Ellison Street, and on the south side followed the line of the stone houses, now shops, and what was then the Albion Hotel.

Robert Hamnett the well-known Glossop Historian of the late 19th and early 20th century describes the lanes and paths in one of his many articles in the Glossop Chronicle of the time.
"Princess Street was formerly two fields; a footpath went through them. I well remember the stiles, one near to Mount Pleasant Chapel, and the other at the exit to Pikes Lane, which in 1871 was a cow-lane to Pikes Farm. During the paving and sewering of this street, the old Roman Road from Melandra to Brough was discovered on the south side of Princess St. It went across the Sandhole to Crosscliffe, part of it is still visible in a field near Bank Street, behind No 1 King Street."

Hamnett also says that Park Terrace owes it name to the fact that the houses overlook 'Pinch Belly Park', where men were employed during the American Civil War of the early 1860's which was locally termed 'the cotton panic'. From 1861 to 1864 no cotton was imported from the southern American states, closing the cotton mills of the area and throwing all the operatives out of work.
Lord Howard and the local Board of Guardians set up schemes to employ as many of the workers as possible and many of our present roads were built. These included North Road, Fauvel Road, and Hall Meadow Road, most of Dinting Road and sections of road down Dinting Vale. Many of the reservoirs round the town were also made at this time and much of the arable land in the valley was drained with fired clay land drains, which can still be found today, The men who were employed getting sand for 1 shilling [or 5 pence in decimal coinage] a day from the area south of the brook gave the site its local name 't'sandhole'

Hamnett also writes,
"George Street Foot Bridge was an ancient bridge, and had been washed down by floods many times."
On February 19th 1902 Lord Howard of Glossop offered to put up a new bridge. His offer was accepted, and on October 1st 1902 the bridge was completed and the approaches to it improved. Hamnett states, in his articles,
"It has proved to be a great public convenience; especially now the Picture Palace has been erected, which is built on the site of the George Street Foundry".
Later a Concrete bridge replaced it.

The Palace Theatre or Electric Palace as it was later called was just one of two place of entertainment in the town centre, as the Theatre Royal stood on the south of the extended market ground, just off Victoria Street.

On the other side of the Glossop Brook the land behind the houses on Chapel Street had a long 'Y' shaped mill pond which was fed from a weir just to the west of Market Street. The metal paddles, which regulated the flow, can still be seen in the stone wall although the dam itself was removed to prevent flooding after the water was no longer needed to power Shepley Mill. The millpond ran under George Street Bridge and this can still be seen next to the Stove Shop.

As Shepley Mill grew in size, what had been a large irregular shaped pond to the west of George Street was made into a butterfly-shaped pond with an overflow weir back to the river, which is still just visible by the George Street Bridge. From this point, as far as the High Street West Bridge, it is noticeable that the brook course is much narrowed by the debris from the demolition of Shepley mill in the 1950's. Many of the window sills and larger stones are visible in the banks on the north side. The water taken from the millpond and used to power the factory passed under Hall's Court and ran back into the brook; its outflow is probably the culvert visible just over the wall in Shrewsbury Street.

The mill pond, the remains of which snake through the Sumner's Wren Nest mill site and behind the new shopping complex, is the original river course to the north of Shrewsbury Street. As with most of the other mill sites the owners used the meandering Glossop Brook and diverted it to suit their needs. The Glossop Brook was dammed with a weir and the water not needed in the millpond was sent straight through the site in a deeper cut between high walls. The removal of these walls in recent years and the fact that water was no longer diverted to fall back to the brook much further down the valley has often resulted in flooding.

By the footbridge is the old Glove Works, later a restaurant and bar, and this stands in the corner between the brook and George Street. Before this, to the north and set back from the brook, stood an iron foundry built by Josiah Swain in 1856. He had previously had a foundry behind the old Swan Inn, High Street East.

The George Street Foundry cast the bollards, and presumably the chains, were that were used to surround Norfolk Square. The foundry afterwards became Blackwell's Foundry. During their occupation an explosion occurred, which alarmed all Glossop; hundreds of people rushed from their homes thinking, from the noise, that the Gas Works had blown up.

In January 1860 after a long argument in the town about the provision of gas street lighting the plan went ahead. Strangely enough, many were against the idea but a vote was taken which eventually and only marginally went in favour of gas street lighting in the town.
On May 6th 1860 both Blackwell's tender for lamp parts and the tender of Messrs. John Shaw and Sons to fit and erect the street lamps were accepted. Each lamp and fittings cost £2 2s. 6d. Some of the streets were lit with gas for the first time on September 9th 1861.

The 'sandhole' became allotments. After the First World War Lord Howard of Glossop gave the land to be made into a public park, as a lasting memorial to the men of Glossopdale who died in the many theatres of war during that conflict. This included his son, Lieutenant The Honourable Philip Granville James Fitzalan Howard of the 1st Battalion of the Welsh Guards, who died of wounds in 1918.

The road, which extended from Market Street, was named after Lord Howard's son and was laid in to join Princess Street at St Mary's Road. Paths which followed some of the old allotment paths were improved and paths and flowerbeds lined the road. Seats were placed at vantage points to give views across the valley to Mouselow and down to Dinting and Mottram. After 1935 Alderman Farnsworth's wife gave the town a number of rustic shelters, to be placed set back from the footpaths, along the south side of the road. These were demolished in the 1960's.